SG181423A1 - Novel antiviral compounds - Google Patents
Novel antiviral compounds Download PDFInfo
- Publication number
- SG181423A1 SG181423A1 SG2012035002A SG2012035002A SG181423A1 SG 181423 A1 SG181423 A1 SG 181423A1 SG 2012035002 A SG2012035002 A SG 2012035002A SG 2012035002 A SG2012035002 A SG 2012035002A SG 181423 A1 SG181423 A1 SG 181423A1
- Authority
- SG
- Singapore
- Prior art keywords
- heterocycle
- alkyl
- alkenyl
- alkynyl
- heteroalkyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 345
- 230000000840 anti-viral effect Effects 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 129
- 239000004480 active ingredient Substances 0.000 claims abstract description 41
- 239000003814 drug Substances 0.000 claims abstract description 36
- 238000011282 treatment Methods 0.000 claims abstract description 36
- 208000036142 Viral infection Diseases 0.000 claims abstract description 26
- 230000009385 viral infection Effects 0.000 claims abstract description 26
- 241001465754 Metazoa Species 0.000 claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- -1 cycloalkynyl Chemical group 0.000 claims description 167
- 125000000217 alkyl group Chemical group 0.000 claims description 102
- 125000003118 aryl group Chemical group 0.000 claims description 92
- 125000003342 alkenyl group Chemical group 0.000 claims description 77
- 125000000304 alkynyl group Chemical group 0.000 claims description 75
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 70
- 125000000623 heterocyclic group Chemical group 0.000 claims description 66
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 45
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 125000005015 aryl alkynyl group Chemical group 0.000 claims description 42
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 41
- 229910052799 carbon Inorganic materials 0.000 claims description 41
- 229910052736 halogen Inorganic materials 0.000 claims description 34
- 150000002367 halogens Chemical class 0.000 claims description 34
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 32
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 25
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 19
- 241000124008 Mammalia Species 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 239000008194 pharmaceutical composition Substances 0.000 claims description 14
- 230000002265 prevention Effects 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 239000003937 drug carrier Substances 0.000 claims description 9
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 7
- 208000015181 infectious disease Diseases 0.000 claims description 5
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- 229920002554 vinyl polymer Polymers 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000005670 ethenylalkyl group Chemical group 0.000 claims description 3
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- 230000010076 replication Effects 0.000 abstract description 8
- 230000001225 therapeutic effect Effects 0.000 abstract description 7
- 208000031886 HIV Infections Diseases 0.000 abstract description 5
- 230000002401 inhibitory effect Effects 0.000 abstract description 5
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- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 abstract description 2
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 92
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 52
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- 239000012535 impurity Substances 0.000 description 38
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 26
- JIYXANPMCJRVKB-UHFFFAOYSA-N methyl 2-(2-tert-butyl-7-chloro-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)pentanoate Chemical compound ClC1=C(C(C(=O)OC)CCC)C(C)=NC2=CC(C(C)(C)C)=NN21 JIYXANPMCJRVKB-UHFFFAOYSA-N 0.000 description 25
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 18
- 229940002612 prodrug Drugs 0.000 description 18
- 239000000651 prodrug Substances 0.000 description 18
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
- 125000001183 hydrocarbyl group Chemical group 0.000 description 17
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 16
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- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 12
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- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 2
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- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
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- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
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- YAEFVUSJQYXMGL-UHFFFAOYSA-N methyl 2-(2-tert-butyl-7-chloro-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-3-phenylpropanoate Chemical compound CC1=NC2=CC(C(C)(C)C)=NN2C(Cl)=C1C(C(=O)OC)CC1=CC=CC=C1 YAEFVUSJQYXMGL-UHFFFAOYSA-N 0.000 description 2
- PAFJCJIARXBJOR-UHFFFAOYSA-N methyl 2-(2-tert-butyl-7-chloro-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-4-methoxybutanoate Chemical compound ClC1=C(C(C(=O)OC)CCOC)C(C)=NC2=CC(C(C)(C)C)=NN21 PAFJCJIARXBJOR-UHFFFAOYSA-N 0.000 description 2
- HINHPWLZFLHHNE-UHFFFAOYSA-N methyl 2-(2-tert-butyl-7-chloro-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate Chemical compound ClC1=C(CC(=O)OC)C(C)=NC2=CC(C(C)(C)C)=NN21 HINHPWLZFLHHNE-UHFFFAOYSA-N 0.000 description 2
- NWDKOIBKPJFCEA-UHFFFAOYSA-N methyl 2-(5-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-6-yl)pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=CC=NN2C=1C1=CC=CC=C1 NWDKOIBKPJFCEA-UHFFFAOYSA-N 0.000 description 2
- IIBYTDPCPGBVPV-UHFFFAOYSA-N methyl 2-(7-chloro-5-methyl-2-phenylpyrazolo[1,5-a]pyrimidin-6-yl)acetate Chemical compound N=1N2C(Cl)=C(CC(=O)OC)C(C)=NC2=CC=1C1=CC=CC=C1 IIBYTDPCPGBVPV-UHFFFAOYSA-N 0.000 description 2
- HAALVARHZCYMTB-UHFFFAOYSA-N methyl 2-(7-chloro-5-methyl-2-propan-2-yl-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)acetate Chemical compound ClC1=C(CC(=O)OC)C(C)=NC2=NC(C(C)C)=NN21 HAALVARHZCYMTB-UHFFFAOYSA-N 0.000 description 2
- AYXLLICAKRTTTG-UHFFFAOYSA-N methyl 2-(7-chloro-5-methyl-2-propylpyrazolo[1,5-a]pyrimidin-6-yl)acetate Chemical compound N1=C(C)C(CC(=O)OC)=C(Cl)N2N=C(CCC)C=C21 AYXLLICAKRTTTG-UHFFFAOYSA-N 0.000 description 2
- VVABMSDTZMVZCJ-UHFFFAOYSA-N methyl 2-(7-chloro-5-methyl-2-propylpyrazolo[1,5-a]pyrimidin-6-yl)pentanoate Chemical compound ClC1=C(C(C(=O)OC)CCC)C(C)=NC2=CC(CCC)=NN21 VVABMSDTZMVZCJ-UHFFFAOYSA-N 0.000 description 2
- HDLZVBCVICISHZ-UHFFFAOYSA-N methyl 2-[2,3,5-trimethyl-7-(4-methylphenyl)imidazo[4,5-b]pyridin-6-yl]acetate Chemical compound COC(=O)CC1=C(C)N=C2N(C)C(C)=NC2=C1C1=CC=C(C)C=C1 HDLZVBCVICISHZ-UHFFFAOYSA-N 0.000 description 2
- HCBLVKLGYJFXNV-UHFFFAOYSA-N methyl 2-[2,3,5-trimethyl-7-(4-methylphenyl)imidazo[4,5-b]pyridin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C1=C(C)N=C2N(C)C(C)=NC2=C1C1=CC=C(C)C=C1 HCBLVKLGYJFXNV-UHFFFAOYSA-N 0.000 description 2
- DPGMIZSZOFBNHX-UHFFFAOYSA-N methyl 2-[2-(furan-2-yl)-5-methyl-7-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=CC(C=3OC=CC=3)=NN2C=1C1=CC=C(C)C=C1 DPGMIZSZOFBNHX-UHFFFAOYSA-N 0.000 description 2
- BGFPXTUNUQXKNS-UHFFFAOYSA-N methyl 2-[2-tert-butyl-3,5-dimethyl-7-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=C(C)C(C(C)(C)C)=NN2C=1C1=CC=C(C)C=C1 BGFPXTUNUQXKNS-UHFFFAOYSA-N 0.000 description 2
- WWCVLBMDGVZPNV-UHFFFAOYSA-N methyl 2-[2-tert-butyl-5-methyl-7-(1-methylindol-5-yl)pyrazolo[1,5-a]pyrimidin-6-yl]-3-phenylpropanoate Chemical compound CC1=NC2=CC(C(C)(C)C)=NN2C(C=2C=C3C=CN(C)C3=CC=2)=C1C(C(=O)OC)CC1=CC=CC=C1 WWCVLBMDGVZPNV-UHFFFAOYSA-N 0.000 description 2
- MYQHCKCFNXRNQN-UHFFFAOYSA-N methyl 2-[2-tert-butyl-5-methyl-7-(1-methylindol-6-yl)pyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound C1=C2C=CN(C)C2=CC(C=2N3N=C(C=C3N=C(C)C=2C(C(=O)OC)CCC)C(C)(C)C)=C1 MYQHCKCFNXRNQN-UHFFFAOYSA-N 0.000 description 2
- SUKUSZPNGOMXCX-UHFFFAOYSA-N methyl 2-[2-tert-butyl-5-methyl-7-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-6-yl]-4-methoxybutanoate Chemical compound COCCC(C(=O)OC)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(C)C=C1 SUKUSZPNGOMXCX-UHFFFAOYSA-N 0.000 description 2
- LGHWMYXWYMFLPH-UHFFFAOYSA-N methyl 2-[2-tert-butyl-5-methyl-7-(4-propan-2-ylphenyl)pyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(C(C)C)C=C1 LGHWMYXWYMFLPH-UHFFFAOYSA-N 0.000 description 2
- HBTXVKUHLOUXIR-UHFFFAOYSA-N methyl 2-[2-tert-butyl-5-methyl-7-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(C(F)(F)F)C=C1 HBTXVKUHLOUXIR-UHFFFAOYSA-N 0.000 description 2
- ZAAZXLHULCOWAF-UHFFFAOYSA-N methyl 2-[2-tert-butyl-7-(1h-indol-5-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound C1=C2NC=CC2=CC(C=2N3N=C(C=C3N=C(C)C=2C(C(=O)OC)CCC)C(C)(C)C)=C1 ZAAZXLHULCOWAF-UHFFFAOYSA-N 0.000 description 2
- QIGJMKVCGDFVCF-UHFFFAOYSA-N methyl 2-[2-tert-butyl-7-(2,3-dihydro-1-benzofuran-5-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound C1=C2OCCC2=CC(C=2N3N=C(C=C3N=C(C)C=2C(C(=O)OC)CCC)C(C)(C)C)=C1 QIGJMKVCGDFVCF-UHFFFAOYSA-N 0.000 description 2
- YIVMGSBHAMMRJM-UHFFFAOYSA-N methyl 2-[2-tert-butyl-7-(2,4-difluorophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(F)C=C1F YIVMGSBHAMMRJM-UHFFFAOYSA-N 0.000 description 2
- BYWLQYDDMNAOIO-UHFFFAOYSA-N methyl 2-[2-tert-butyl-7-(2,4-dimethylphenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(C)C=C1C BYWLQYDDMNAOIO-UHFFFAOYSA-N 0.000 description 2
- CZKGLBDANODSRF-UHFFFAOYSA-N methyl 2-[2-tert-butyl-7-(2-chloro-4-methylphenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(C)C=C1Cl CZKGLBDANODSRF-UHFFFAOYSA-N 0.000 description 2
- LALWJPNZMRVJGW-UHFFFAOYSA-N methyl 2-[2-tert-butyl-7-(2-fluoro-4-methoxyphenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(OC)C=C1F LALWJPNZMRVJGW-UHFFFAOYSA-N 0.000 description 2
- XVFMHYAIDHRUNX-UHFFFAOYSA-N methyl 2-[2-tert-butyl-7-(2-fluoro-4-methylphenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(C)C=C1F XVFMHYAIDHRUNX-UHFFFAOYSA-N 0.000 description 2
- QATOMVKYNAQJHE-UHFFFAOYSA-N methyl 2-[2-tert-butyl-7-(3,4-dihydro-2h-1,5-benzodioxepin-7-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound O1CCCOC2=CC(C=3N4N=C(C=C4N=C(C)C=3C(C(=O)OC)CCC)C(C)(C)C)=CC=C21 QATOMVKYNAQJHE-UHFFFAOYSA-N 0.000 description 2
- PBVUFXFSCIBPFM-UHFFFAOYSA-N methyl 2-[2-tert-butyl-7-(3,4-dihydro-2h-chromen-6-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound O1CCCC2=CC(C=3N4N=C(C=C4N=C(C)C=3C(C(=O)OC)CCC)C(C)(C)C)=CC=C21 PBVUFXFSCIBPFM-UHFFFAOYSA-N 0.000 description 2
- ZVIIAYXMQYBWRR-UHFFFAOYSA-N methyl 2-[2-tert-butyl-7-(4-chloro-2-methoxyphenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=CC(C(C)(C)C)=NN2C=1C1=CC=C(Cl)C=C1OC ZVIIAYXMQYBWRR-UHFFFAOYSA-N 0.000 description 2
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- MWZMBQOCFUAUJT-UHFFFAOYSA-N methyl 2-[5-methyl-7-(4-methylphenyl)-2-phenylpyrazolo[1,5-a]pyrimidin-6-yl]pentanoate Chemical compound CCCC(C(=O)OC)C=1C(C)=NC2=CC(C=3C=CC=CC=3)=NN2C=1C1=CC=C(C)C=C1 MWZMBQOCFUAUJT-UHFFFAOYSA-N 0.000 description 2
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- KKRYDPVDJYCEER-QEGGNFSNSA-N tert-butyl n-[(2s,3r)-3-hydroxy-4-[[(2r,3s)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-phenylbutyl]amino]-1-phenylbutan-2-yl]carbamate Chemical compound C([C@H](NC(=O)OC(C)(C)C)[C@H](O)CNC[C@@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)OC(C)(C)C)C1=CC=CC=C1 KKRYDPVDJYCEER-QEGGNFSNSA-N 0.000 description 1
- DZUIFTBFVIXAMZ-YHKVADFHSA-N tert-butyl n-[(2s,3s,5r)-3-hydroxy-5-[(4-methoxyphenyl)methyl]-6-[[(2s)-3-methyl-1-[[(2s)-1-morpholin-4-yl-1-oxo-3-phenylpropan-2-yl]amino]-1-oxobutan-2-yl]amino]-6-oxo-1-phenylhexan-2-yl]carbamate Chemical compound C1=CC(OC)=CC=C1C[C@@H](C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N1CCOCC1)C[C@H](O)[C@@H](NC(=O)OC(C)(C)C)CC1=CC=CC=C1 DZUIFTBFVIXAMZ-YHKVADFHSA-N 0.000 description 1
- NAJDZKGRZBLNON-RKGCBODKSA-N tert-butyl n-[(2s,3s,5r)-5-benzyl-3-hydroxy-6-[[(2s)-3-methyl-1-[[(2s)-1-morpholin-4-yl-1-oxo-3-phenylpropan-2-yl]amino]-1-oxobutan-2-yl]amino]-6-oxo-1-phenylhexan-2-yl]carbamate Chemical compound C([C@@H]([C@@H](O)C[C@H](C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N1CCOCC1)CC=1C=CC=CC=1)NC(=O)OC(C)(C)C)C1=CC=CC=C1 NAJDZKGRZBLNON-RKGCBODKSA-N 0.000 description 1
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
- 239000012414 tert-butyl nitrite Substances 0.000 description 1
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- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
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- 125000004927 thianaphthalenyl group Chemical group S1C(C=CC2=CC=CC=C12)* 0.000 description 1
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- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
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- ZFEAMMNVDPDEGE-LGRGJMMZSA-N tifuvirtide Chemical compound C([C@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(C)=O)[C@@H](C)CC)[C@@H](C)O)[C@@H](C)CC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)C1=CC=C(O)C=C1 ZFEAMMNVDPDEGE-LGRGJMMZSA-N 0.000 description 1
- 229960000838 tipranavir Drugs 0.000 description 1
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- 231100000440 toxicity profile Toxicity 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
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- 125000004306 triazinyl group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 229960001082 trimethoprim Drugs 0.000 description 1
- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- NOYPYLRCIDNJJB-UHFFFAOYSA-N trimetrexate Chemical compound COC1=C(OC)C(OC)=CC(NCC=2C(=C3C(N)=NC(N)=NC3=CC=2)C)=C1 NOYPYLRCIDNJJB-UHFFFAOYSA-N 0.000 description 1
- 229960001099 trimetrexate Drugs 0.000 description 1
- DFHAXXVZCFXGOQ-UHFFFAOYSA-K trisodium phosphonoformate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)P([O-])([O-])=O DFHAXXVZCFXGOQ-UHFFFAOYSA-K 0.000 description 1
- YFNGWGVTFYSJHE-UHFFFAOYSA-K trisodium;phosphonoformate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)C([O-])=O.OP(O)(=O)C([O-])=O.OP(O)(=O)C([O-])=O YFNGWGVTFYSJHE-UHFFFAOYSA-K 0.000 description 1
- 229940111527 trizivir Drugs 0.000 description 1
- WVPSKSLAZQPAKQ-CDMJZVDBSA-N trovafloxacin Chemical compound C([C@H]1[C@@H]([C@H]1C1)N)N1C(C(=CC=1C(=O)C(C(O)=O)=C2)F)=NC=1N2C1=CC=C(F)C=C1F WVPSKSLAZQPAKQ-CDMJZVDBSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Virology (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0922520A GB0922520D0 (en) | 2009-12-23 | 2009-12-23 | Novel antiviral compounds |
| GBGB1001204.5A GB201001204D0 (en) | 2010-01-26 | 2010-01-26 | Novel antiviral compounds |
| PCT/EP2010/070306 WO2011076765A1 (fr) | 2009-12-23 | 2010-12-20 | Nouveaux composés antiviraux |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SG181423A1 true SG181423A1 (en) | 2012-07-30 |
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| Application Number | Title | Priority Date | Filing Date |
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| SG10201408512RA SG10201408512RA (en) | 2009-12-23 | 2010-12-20 | Novel antiviral compounds |
| SG2012035002A SG181423A1 (en) | 2009-12-23 | 2010-12-20 | Novel antiviral compounds |
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| Application Number | Title | Priority Date | Filing Date |
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| SG10201408512RA SG10201408512RA (en) | 2009-12-23 | 2010-12-20 | Novel antiviral compounds |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US20120316161A1 (fr) |
| EP (1) | EP2516008B1 (fr) |
| JP (1) | JP2013515692A (fr) |
| KR (1) | KR101483834B1 (fr) |
| CN (1) | CN102770181B (fr) |
| AU (1) | AU2010334958B2 (fr) |
| CA (1) | CA2781780C (fr) |
| ES (1) | ES2475970T3 (fr) |
| IL (1) | IL219965A0 (fr) |
| MX (1) | MX2012007410A (fr) |
| PT (1) | PT2516008E (fr) |
| SG (2) | SG10201408512RA (fr) |
| WO (1) | WO2011076765A1 (fr) |
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| GB0908394D0 (en) | 2009-05-15 | 2009-06-24 | Univ Leuven Kath | Novel viral replication inhibitors |
| GB0913636D0 (en) | 2009-08-05 | 2009-09-16 | Univ Leuven Kath | Novel viral replication inhibitors |
| US9102614B2 (en) | 2010-07-02 | 2015-08-11 | Gilead Sciences, Inc. | Naphth-2-ylacetic acid derivatives to treat AIDS |
| JP5806735B2 (ja) | 2010-07-02 | 2015-11-10 | ギリアード サイエンシーズ， インコーポレイテッド | Ｈｉｖ抗ウイルス化合物としての２−キノリニル−酢酸誘導体 |
| US8633200B2 (en) | 2010-09-08 | 2014-01-21 | Bristol-Myers Squibb Company | Inhibitors of human immunodeficiency virus replication |
| AU2011331301A1 (en) | 2010-11-15 | 2013-05-23 | Katholieke Universiteit Leuven | Antiviral condensed heterocyclic compounds |
| WO2012066442A1 (fr) | 2010-11-15 | 2012-05-24 | Pfizer Limited | Inhibiteurs de la réplication du vih |
| EP2511273B8 (fr) | 2011-04-15 | 2019-06-26 | Hivih | Inhibiteurs de la réplication virale, leur procédé de préparation et leurs utilisations thérapeutiques |
| AP2015008931A0 (en) | 2011-04-21 | 2015-12-31 | Gilead Sciences Inc | Benzothiazole compounds and their pharmaceutical use |
| US8791108B2 (en) | 2011-08-18 | 2014-07-29 | Bristol-Myers Squibb Company | Inhibitors of human immunodeficiency virus replication |
| JP6099149B2 (ja) | 2011-10-25 | 2017-03-22 | 塩野義製薬株式会社 | Ｈｉｖ複製阻害剤 |
| AU2012358805B2 (en) * | 2011-12-22 | 2017-07-20 | Gilead Sciences, Inc. | Pyrazolo[1,5-a]pyrimidines as antiviral agents |
| US9284323B2 (en) | 2012-01-04 | 2016-03-15 | Gilead Sciences, Inc. | Naphthalene acetic acid derivatives against HIV infection |
| WO2013103724A1 (fr) | 2012-01-04 | 2013-07-11 | Gilead Sciences, Inc. | Dérivés d'acide 2-(tert-butoxy)-2-(7-méthylquinoléin-6-yl)acétique pour traiter le sida |
| US8629276B2 (en) | 2012-02-15 | 2014-01-14 | Bristol-Myers Squibb Company | Inhibitors of human immunodeficiency virus replication |
| US9034882B2 (en) * | 2012-03-05 | 2015-05-19 | Bristol-Myers Squibb Company | Inhibitors of human immunodeficiency virus replication |
| US9006235B2 (en) | 2012-03-06 | 2015-04-14 | Bristol-Myers Squibb Company | Inhibitors of human immunodeficiency virus replication |
| UY34750A (es) | 2012-04-20 | 2013-11-29 | Gilead Sciences Inc | ?compuestos para el tratamiento del hiv, composiciones,métodos de preparación, intermediarios y métodos terapéuticos?. |
| US8906929B2 (en) | 2012-08-16 | 2014-12-09 | Bristol-Myers Squibb Company | Inhibitors of human immunodeficiency virus replication |
| EP2719685A1 (fr) | 2012-10-11 | 2014-04-16 | Laboratoire Biodim | Inhibiteurs de la réplication virale, leur procédé de préparation et leurs utilisations thérapeutiques |
| TW201441197A (zh) | 2013-01-31 | 2014-11-01 | Shionogi & Co | Ｈｉｖ複製抑制劑 |
| EP2970301B1 (fr) | 2013-03-13 | 2017-01-11 | VIIV Healthcare UK (No.5) Limited | Inhibiteurs de la réplication du virus de l'immunodéficience humaine |
| US9580431B2 (en) * | 2013-03-13 | 2017-02-28 | VIIV Healthcare UK (No.5) Limited | Inhibitors of human immunodeficiency virus replication |
| EP2970273B1 (fr) | 2013-03-13 | 2017-03-01 | VIIV Healthcare UK (No.5) Limited | Inhibiteurs de la réplication du virus de l'immunodéficience humaine |
| WO2014159076A1 (fr) | 2013-03-14 | 2014-10-02 | Bristol-Myers Squibb Company | Inhibiteurs de la réplication du virus de l'immunodéficience humaine |
| ES2623904T3 (es) | 2013-03-14 | 2017-07-12 | VIIV Healthcare UK (No.5) Limited | Inhibidores de la replicación del virus de la inmunodeficiencia humana |
| EP2821082A1 (fr) | 2013-07-05 | 2015-01-07 | Laboratoire Biodim | Procédé de production d'un lentivirus inactivé, notamment le VIH, vaccin, kit et procédé d'utilisation |
| WO2015119249A1 (fr) | 2014-02-07 | 2015-08-13 | 国立大学法人東京医科歯科大学 | Accélérateur de myogenèse, suppresseur d'amyotrophie, composition médicinale et activateur de taz |
| EP3105236B1 (fr) | 2014-02-12 | 2017-10-18 | ViiV Healthcare UK (No.5) Limited | Utilisation de macrocycles de benzothiazole comme qu'inhibiteurs de la réplication du virus de l'immunodéficience humaine |
| WO2015123182A1 (fr) * | 2014-02-12 | 2015-08-20 | Bristol-Myers Squibb Company | Macrocycles de pyrazolopyrimidine utilisés en tant qu'inhibiteurs de la réplication du virus de l'immunodéficience humaine |
| US9932353B2 (en) | 2014-02-18 | 2018-04-03 | Viiv Healthcare Uk (No. 5) Limited | Imidazopyrimidine macrocycles as inhibitors of human immunodeficiency virus replication |
| WO2015126743A1 (fr) | 2014-02-18 | 2015-08-27 | Bristol-Myers Squibb Company | Macrocycles de pyrazolopyrimidine utilisés en tant qu'inhibiteurs de la réplication du virus de l'immunodéficience humaine |
| US9409922B2 (en) | 2014-02-18 | 2016-08-09 | Bristol-Myers Squibb Company | Imidazopyridine macrocycles as inhibitors of human immunodeficiency virus replication |
| US9273067B2 (en) | 2014-02-19 | 2016-03-01 | Bristol-Myers Squibb Company | Pyrazolopyrimidine macrocycles as inhibitors of human immunodeficiency virus replication |
| PT3107913T (pt) | 2014-02-19 | 2018-09-28 | Viiv Healthcare Uk No 5 Ltd | Inibidores da replicação do vírus da imunodeficiência humana |
| US9637501B2 (en) | 2014-02-20 | 2017-05-02 | Viiv Healthcare Uk (No. 5) Limited | Pyridin-3-yl acetic acid macrocycles as inhibitors of human immunodeficiency virus replication |
| US9193720B2 (en) | 2014-02-20 | 2015-11-24 | Bristol-Myers Squibb Company | Pyridin-3-yl acetic acid derivatives as inhibitors of human immunodeficiency virus replication |
| JP6579549B2 (ja) | 2014-05-16 | 2019-09-25 | 塩野義製薬株式会社 | Ｈｉｖ複製阻害作用を有する３環性複素環誘導体 |
| KR101692478B1 (ko) | 2014-07-10 | 2017-01-05 | 계명대학교 산학협력단 | Ｓｙ０２９를 유효성분으로 함유하는 항바이러스 조성물 |
| CN107922423B (zh) | 2015-05-29 | 2020-10-27 | 盐野义制药株式会社 | 具有hiv复制抑制作用的含氮三环性衍生物 |
| JP2018520162A (ja) | 2015-07-06 | 2018-07-26 | ヴィーブ ヘルスケア ユーケー（ナンバー５）リミテッド | ヒト免疫不全ウイルス複製の阻害剤としてのピリジン−３−イル酢酸誘導体 |
| CN107835808A (zh) | 2015-07-08 | 2018-03-23 | Viiv保健英国第五有限公司 | 作为人类免疫缺陷性病毒复制的抑制剂的吡啶‑3‑基乙酸衍生物 |
| WO2017006280A1 (fr) | 2015-07-09 | 2017-01-12 | VIIV Healthcare UK (No.5) Limited | Dérivés de l'acide pyridin-3-yl-acétique utilisés comme inhibiteurs de la réplication du virus de l'immunodéficience humaine |
| AU2016290986A1 (en) | 2015-07-09 | 2018-01-18 | VIIV Healthcare UK (No.5) Limited | Pyridin-3-yl acetic acid derivatives as inhibitors of human immunodeficiency virus replication |
| CA2994512A1 (fr) | 2015-08-07 | 2017-02-16 | VIIV Healthcare UK (No.5) Limited | Derives d'acide pyridin-3-yl acetique comme inhibiteurs de la replication du virus de l'immunodeficience humaine |
| EP3334741A1 (fr) | 2015-08-10 | 2018-06-20 | VIIV Healthcare UK (No.5) Limited | Macrocycles d'imidazopyridine en tant qu'inhibiteurs de la réplication du virus de l'immunodéficience humaine |
| TWI657086B (zh) | 2015-08-11 | 2019-04-21 | 英商Viiv醫療保健英國(No.5)有限公司 | 做為人類免疫缺陷病毒複製抑制劑之５－（ｎ－苯甲基四氫異喹啉－６－基）吡啶－３－基乙酸衍生物 |
| CA2995042A1 (fr) | 2015-08-12 | 2017-02-16 | VIIV Healthcare UK (No.5) Limited | Derives bicycliques condenses d'acide 5-(n- [6,5]-aryle tetrahydroisoquinolin-6-yl) pyridin-3-yl-acetique utilises en tant qu'inhibiteurs de la replication du virus de l'immunodeficience humaine |
| TW201718537A (zh) | 2015-08-12 | 2017-06-01 | Ｖｉｉｖ醫療保健英國（Ｎｏ．５）有限公司 | 做為人類免疫缺陷病毒複製抑制劑之吡啶－３－基乙酸衍生物 |
| AU2016305339A1 (en) | 2015-08-12 | 2018-03-01 | VIIV Healthcare UK (No.5) Limited | 5-(n-fused tricyclic Aryl tetrahydroisoquinolin-6-yl) pyridin-3- yl acetic acid derivatives as inhibitors of Human Immunodeficiency Virus replication |
| US10106504B2 (en) | 2015-08-20 | 2018-10-23 | VIIV Healthcare UK (No.5) Limited | Pyridin-3-yl acetic acid derivatives as inhibitors of human immunodeficiency virus replication |
| EP3455217A1 (fr) | 2016-05-11 | 2019-03-20 | ViiV Healthcare UK (No.5) Limited | Dérivés d'acide pyridin-3-yle acétique utilisés comme inhibiteurs de la réplication du virus de l'immunodéficience humaine |
| EP3455214A1 (fr) | 2016-05-11 | 2019-03-20 | ViiV Healthcare UK (No.5) Limited | Dérivés d'acide pyridin-3-yle acétique utilisés comme inhibiteurs de la réplication du virus de l'immunodéficience humaine |
| WO2017195113A1 (fr) | 2016-05-11 | 2017-11-16 | VIIV Healthcare UK (No.5) Limited | Dérivés d'acide pyridin-3-yle acétique utilisés comme inhibiteurs de la réplication du virus de l'immunodéficience humaine |
| EP3565810A1 (fr) | 2017-01-03 | 2019-11-13 | ViiV Healthcare UK (No.5) Limited | Dérivés d'acide pyridin-3-yle acétique utilisés en tant qu'inhibiteurs de la réplication du virus de l'immunodéficience humaine |
| JP2020503348A (ja) | 2017-01-03 | 2020-01-30 | ヴィーブ ヘルスケア ユーケー（ナンバー５）リミテッド | ヒト免疫不全ウイルス複製の阻害剤としてのピリジン−３−イル酢酸誘導体 |
| WO2019244066A2 (fr) | 2018-06-19 | 2019-12-26 | VIIV Healthcare UK (No.5) Limited | Dérivés d'acide pyridin-3-yl-acétique en tant qu'inhibiteurs de la réplication du virus de l'immunodéficience humaine |
| WO2020003093A1 (fr) | 2018-06-25 | 2020-01-02 | VIIV Healthcare UK (No.5) Limited | Dérivés d'acide pyridin-3-yl-acétique en tant qu'inhibiteurs de la réplication du virus de l'immunodéficience humaine |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE174917T1 (de) * | 1991-04-22 | 1999-01-15 | Otsuka Pharma Co Ltd | Pyrazolo(1,5-a>pyrimidinderivate und sie enthaltende antiinflammatorische mittel |
| US5543523A (en) | 1994-11-15 | 1996-08-06 | Regents Of The University Of Minnesota | Method and intermediates for the synthesis of korupensamines |
| CN1659143A (zh) * | 2001-03-01 | 2005-08-24 | 盐野义制药株式会社 | 具有hiv整合酶抑制活性的含氮杂芳基化合物 |
| JP2003171381A (ja) | 2001-09-25 | 2003-06-20 | Takeda Chem Ind Ltd | エントリー阻害剤 |
| JP2003119137A (ja) | 2001-10-10 | 2003-04-23 | Japan Tobacco Inc | Ｈｉｖ阻害剤 |
| DE60218511T2 (de) | 2001-10-26 | 2007-10-25 | Istituto Di Richerche Di Biologia Molecolare P. Angeletti S.P.A. | Dihydroxypyrimidin-carbonsäueramid-hemmer der hiv-integrase |
| AU2002349675A1 (en) | 2001-12-05 | 2003-06-17 | Shionogi And Co., Ltd. | Derivative having hiv integrase inhibitory activity |
| JP2005515206A (ja) | 2001-12-12 | 2005-05-26 | ブリストル−マイヤーズ スクイブ カンパニー | Ｈｉｖインテグラーゼ・インヒビター |
| BR0215260A (pt) | 2001-12-21 | 2004-12-07 | Tibotec Pharm Ltd | Inibidores de hiv protease de sulfonamida contendo fenila substituìda heterocìclica de amplo espectro |
| JP4523281B2 (ja) | 2002-01-17 | 2010-08-11 | メルク・シャープ・エンド・ドーム・コーポレイション | Ｈｉｖインテグラーゼ阻害薬として有用なヒドロキシナフチリジノンカルボキサミド類 |
| TW200306192A (en) | 2002-01-18 | 2003-11-16 | Bristol Myers Squibb Co | Tricyclic 2-pyrimidone compounds useful as HIV reverse transcriptase inhibitors |
| US7449488B2 (en) | 2002-06-04 | 2008-11-11 | Schering Corporation | Pyrazolopyrimidines as protein kinase inhibitors |
| PA8586801A1 (es) * | 2002-10-31 | 2005-02-04 | Pfizer | Inhibidores de hiv-integrasa, composiciones farmaceuticas y metodos para su uso |
| EP2220084B1 (fr) * | 2007-11-16 | 2014-02-19 | Gilead Sciences, Inc. | Inhibiteurs de la réplication du virus de l'immunodéficience humaine |
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2010
- 2010-12-20 AU AU2010334958A patent/AU2010334958B2/en not_active Ceased
- 2010-12-20 CA CA2781780A patent/CA2781780C/fr not_active Expired - Fee Related
- 2010-12-20 MX MX2012007410A patent/MX2012007410A/es active IP Right Grant
- 2010-12-20 KR KR1020127019420A patent/KR101483834B1/ko not_active IP Right Cessation
- 2010-12-20 CN CN201080064636.2A patent/CN102770181B/zh not_active Expired - Fee Related
- 2010-12-20 EP EP10801407.7A patent/EP2516008B1/fr not_active Not-in-force
- 2010-12-20 SG SG10201408512RA patent/SG10201408512RA/en unknown
- 2010-12-20 JP JP2012545282A patent/JP2013515692A/ja not_active Ceased
- 2010-12-20 WO PCT/EP2010/070306 patent/WO2011076765A1/fr active Application Filing
- 2010-12-20 US US13/518,434 patent/US20120316161A1/en not_active Abandoned
- 2010-12-20 PT PT108014077T patent/PT2516008E/pt unknown
- 2010-12-20 ES ES10801407.7T patent/ES2475970T3/es active Active
- 2010-12-20 SG SG2012035002A patent/SG181423A1/en unknown
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2012
- 2012-05-23 IL IL219965A patent/IL219965A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN102770181A (zh) | 2012-11-07 |
| CN102770181B (zh) | 2015-08-12 |
| EP2516008A1 (fr) | 2012-10-31 |
| PT2516008E (pt) | 2014-07-16 |
| US20120316161A1 (en) | 2012-12-13 |
| IL219965A0 (en) | 2012-07-31 |
| WO2011076765A1 (fr) | 2011-06-30 |
| SG10201408512RA (en) | 2015-02-27 |
| AU2010334958B2 (en) | 2015-02-05 |
| EP2516008B1 (fr) | 2014-04-16 |
| KR20120106869A (ko) | 2012-09-26 |
| CA2781780A1 (fr) | 2011-06-30 |
| AU2010334958A1 (en) | 2012-06-07 |
| JP2013515692A (ja) | 2013-05-09 |
| MX2012007410A (es) | 2012-07-17 |
| CA2781780C (fr) | 2015-02-17 |
| KR101483834B1 (ko) | 2015-01-16 |
| ES2475970T3 (es) | 2014-07-11 |
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